Search results

Search for "glycosylation" in Full Text gives 174 result(s) in Beilstein Journal of Organic Chemistry.

Introduction of a human- and keyboard-friendly N-glycan nomenclature

  • Friedrich Altmann,
  • Johannes Helm,
  • Martin Pabst and
  • Johannes Stadlmann

Beilstein J. Org. Chem. 2024, 20, 607–620, doi:10.3762/bjoc.20.53

Graphical Abstract
  • greatly facilitate keyboard-based mining for glycan substructures in glycan repositories. Keywords: N-glycans; nomenclature; structural features; Introduction Virtually any article on protein glycosylation starts with imposing assurances about the biological significance of the various structures. This
  • “proglycan” nomenclature, an acronym derived from our then nom de guerre “protein-glycosylation analysis” group. By the way, glycan analysis also funneled in activities in the area of allergy diagnosis, where the term MUXF3 enjoys widespread use [38][39][40]. Finally, our work on the isomer-specific analysis
PDF
Album
Supp Info
Perspective
Published 15 Mar 2024

Elucidating the glycan-binding specificity and structure of Cucumis melo agglutinin, a new R-type lectin

  • Jon Lundstrøm,
  • Emilie Gillon,
  • Valérie Chazalet,
  • Nicole Kerekes,
  • Antonio Di Maio,
  • Ten Feizi,
  • Yan Liu,
  • Annabelle Varrot and
  • Daniel Bojar

Beilstein J. Org. Chem. 2024, 20, 306–320, doi:10.3762/bjoc.20.31

Graphical Abstract
  • profiling, thereby advancing both diagnostic methods and biomarker discovery. Examples include arrays that can rapidly profile alterations in glycosylation patterns, pivotal in many diseases and inflammatory changes [10][11]. Traditionally, lectins are divided into classes based on structural similarity and
  • ). In parallel, we also expressed CMA1 in a bacterial expression system, which allowed us to ascertain whether binding was influenced by lectin glycosylation. The full-length mature protein (6–264) and individual N- or C-terminal domains were expressed using a N-terminal fusion comprising DsbC and a
  • binding in solution and a further confirmation of the binding specificity obtained by the array experiments. We note that the functional activity of bacterially produced CMA1 indicates that potential modification by glycosylation is not required for ligand binding. Next, we set out to quantify the binding
PDF
Album
Supp Info
Full Research Paper
Published 19 Feb 2024

Optimizations of lipid II synthesis: an essential glycolipid precursor in bacterial cell wall synthesis and a validated antibiotic target

  • Milandip Karak,
  • Cian R. Cloonan,
  • Brad R. Baker,
  • Rachel V. K. Cochrane and
  • Stephen A. Cochrane

Beilstein J. Org. Chem. 2024, 20, 220–227, doi:10.3762/bjoc.20.22

Graphical Abstract
  • bacteria. Accessing this valuable cell wall precursor is important both for studying cell wall synthesis and for studying/identifying novel antimicrobial compounds. Herein, we describe optimizations to the modular chemical synthesis of lipid II and unnatural analogues. In particular, the glycosylation step
  • analogues through the incorporation of alternative building blocks at different stages of synthesis. Keywords: chemical glycosylation; lipid II; peptidoglycan; polyprenyls; total synthesis; Introduction Lipid II (Figure 1) is an essential bacterial glycolipid involved in peptidoglycan biosynthesis [1]. It
  • describe herein. The base lipid II syntheses upon which optimizations were made are our previously reported syntheses of Gram-negative lipid II in 2016 [20] and Gram-positive lipid II (11) in 2018 [23]. Building upon these synthetic strategies we have achieved noteworthy enhancements in glycosylation
PDF
Album
Supp Info
Full Research Paper
Published 06 Feb 2024

Comparison of glycosyl donors: a supramer approach

  • Anna V. Orlova,
  • Nelly N. Malysheva,
  • Maria V. Panova,
  • Nikita M. Podvalnyy,
  • Michael G. Medvedev and
  • Leonid O. Kononov

Beilstein J. Org. Chem. 2024, 20, 181–192, doi:10.3762/bjoc.20.18

Graphical Abstract
  • , Russian Federation 10.3762/bjoc.20.18 Abstract The development of new methods for chemical glycosylation commonly includes comparison of various glycosyl donors. An attempted comparison of chemical properties of two sialic acid-based thioglycoside glycosyl donors, differing only in the substituent at O-9
  • (trifluoroacetyl vs chloroacetyl), at different concentrations (0.05 and 0.15 mol·L−1) led to mutually excluding conclusions concerning their relative reactivity and selectivity, which prevented us from revealing a possible influence of remote protective groups at O-9 on glycosylation outcome. According to the
  • and straightforward as it is usually considered. Keywords: concentration; glycosylation; protecting groups; reactivity; sialic acids; stereoselectivity; Introduction Glycoconjugates containing sialic acid occur on the surface of all cell types in a variety of organisms. They participate in a broad
PDF
Album
Supp Info
Full Research Paper
Published 31 Jan 2024

Synthesis of the 3’-O-sulfated TF antigen with a TEG-N3 linker for glycodendrimersomes preparation to study lectin binding

  • Mark Reihill,
  • Hanyue Ma,
  • Dennis Bengtsson and
  • Stefan Oscarson

Beilstein J. Org. Chem. 2024, 20, 173–180, doi:10.3762/bjoc.20.17

Graphical Abstract
  • glycosylation reactions. The 3’-sulfate was finally introduced through tin activation in benzene/DMF followed by treatment with a sulfur trioxide–trimethylamine complex in a 66% yield. Keywords: regioselective sulfation; thioglycoside donors; Thomsen–Friedenreich antigen; Introduction In a collaboration
  • at this stage was predicted to be problematic. Therefore, the azido functionality was installed in the spacer before the glycosylation. Donor 3 underwent an NIS/AgOTf-promoted glycosylation with the TEG-N3 acceptor [18], furnishing α-linked 4 in an 85% yield (Scheme 1). H-1 appeared as a doublet at
  • choice [12], surprisingly better than a benzoylated donor [19], why this donor was the first one tested also with the quite different acceptor 5. An NIS/AgOTf-promoted glycosylation with donor 6 [20] yielded 79% of disaccharide 7. Due to the presence of rotamers, NMR spectra of 7 proved to be difficult
PDF
Album
Supp Info
Full Research Paper
Published 30 Jan 2024

Synthesis of ether lipids: natural compounds and analogues

  • Marco Antônio G. B. Gomes,
  • Alicia Bauduin,
  • Chloé Le Roux,
  • Romain Fouinneteau,
  • Wilfried Berthe,
  • Mathieu Berchel,
  • Hélène Couthon and
  • Paul-Alain Jaffrès

Beilstein J. Org. Chem. 2023, 19, 1299–1369, doi:10.3762/bjoc.19.96

Graphical Abstract
PDF
Album
Review
Published 08 Sep 2023

Linker, loading, and reaction scale influence automated glycan assembly

  • Marlene C. S. Dal Colle,
  • Manuel G. Ricardo,
  • Nives Hribernik,
  • José Danglad-Flores,
  • Peter H. Seeberger and
  • Martina Delbianco

Beilstein J. Org. Chem. 2023, 19, 1015–1020, doi:10.3762/bjoc.19.77

Graphical Abstract
  • (BBs) [1][2]. Iterative cycles of glycosylation, capping, and selective deprotection afford the support-bound glycan with a programmable sequence (Figure 1A). The protected glycan is then cleaved from the solid support and subjected to post-AGA deprotection steps to reveal the target glycan. AGA is
  • , but isolated in relatively low yields. The optimization procedures are focused on glycan elongation (i.e., glycosylation and deprotection steps), whereas less attention is given to variables associated with the solid support [17]. In contrast, substantial knowledge exists on how loading [18], reaction
  • increasing order of complexity, we prepared α-1,6-linked dimannosides (1,2) [32], branched trisaccharides (3,4) [12], and linear α-1,4-linked hexaglucosides (5,6) [15][33]. Each synthesis was performed with 6.5 equivalents of BB per glycosylation cycle using previously reported AGA conditions (see Supporting
PDF
Album
Supp Info
Letter
Published 06 Jul 2023

Total synthesis of grayanane natural products

  • Nicolas Fay,
  • Rémi Blieck,
  • Cyrille Kouklovsky and
  • Aurélien de la Torre

Beilstein J. Org. Chem. 2022, 18, 1707–1719, doi:10.3762/bjoc.18.181

Graphical Abstract
  • transformations include the removal of the ketone on the C ring, epoxide reductive opening, formation of the B ring exo-olefin, and glycosylation. In 2021, Hong et al. presented a synthetic effort focused on the synthesis of rhodojaponin III B–C rings [40]. The authors employed a Mn(III)-mediated intramolecular
PDF
Album
Review
Published 12 Dec 2022

Synthesis of protected precursors of chitin oligosaccharides by electrochemical polyglycosylation of thioglycosides

  • Md Azadur Rahman,
  • Kana Kuroda,
  • Hirofumi Endo,
  • Norihiko Sasaki,
  • Tomoaki Hamada,
  • Hiraku Sakai and
  • Toshiki Nokami

Beilstein J. Org. Chem. 2022, 18, 1133–1139, doi:10.3762/bjoc.18.117

Graphical Abstract
  • electrochemical polyglycosylation is also discussed, based on the oxidation potential of the monomer and oligosaccharides. Keywords: electrochemical glycosylation; glucosamine; oligosaccharide; oxidation potential; polyglycosylation; Introduction Chitin oligosaccharides are partial structures of chitin, which
  • from natural sources or by synthesis via chemical glycosylation [2]. Total syntheses of chitin and chitosan oligosaccharides based on conventional chemical glycosylation of protected monosaccharides as building blocks have already been reported. Convergent synthesis using oligosaccharide building
  • blocks can reduce the number of steps in the total synthesis. However, it requires manipulation of the anomeric leaving groups and deprotection of the protected hydroxy group at the 4-position prior to glycosylation. Although automated electrochemical assembly, which is a one-pot iterative synthesis of
PDF
Album
Supp Info
Full Research Paper
Published 30 Aug 2022

Isolation and biosynthesis of daturamycins from Streptomyces sp. KIB-H1544

  • Yin Chen,
  • Jinqiu Ren,
  • Ruimin Yang,
  • Jie Li,
  • Sheng-Xiong Huang and
  • Yijun Yan

Beilstein J. Org. Chem. 2022, 18, 1009–1016, doi:10.3762/bjoc.18.101

Graphical Abstract
  • condensation between two molecules of α-keto acid. Structurally diverse p-terphenyls are formed from these key intermediates by several tailoring reactions such as cyclization, tautomerization, methylation, and glycosylation. A previous study has shown that the formation of 2,5-diarylcyclopentenone proceeds
PDF
Album
Supp Info
Full Research Paper
Published 09 Aug 2022

GlycoBioinformatics

  • Kiyoko F. Aoki-Kinoshita,
  • Frédérique Lisacek,
  • Niclas Karlsson,
  • Daniel Kolarich and
  • Nicolle H. Packer

Beilstein J. Org. Chem. 2021, 17, 2726–2728, doi:10.3762/bjoc.17.184

Graphical Abstract
  • article by Barnett et al. [2] uses molecular dynamics to show that O-linked glycosylation alters peptide conformation, which influences the binding of the peptides to antibodies, despite the fact that glycans are not directly involved in the binding. Another molecular modeling article by Fogarty et al. [3
  • one of the authors of this article, Fadda, used glyco-adapted molecular dynamics to explain in a separate publication [4] how the COVID-19 spike protein recognition element requires N-linked glycosylation to be exposed. Another approach to understanding glyco-interactions is described in a review
PDF
Editorial
Published 09 Nov 2021

Synthetic strategies toward 1,3-oxathiolane nucleoside analogues

  • Umesh P. Aher,
  • Dhananjai Srivastava,
  • Girij P. Singh and
  • Jayashree B. S

Beilstein J. Org. Chem. 2021, 17, 2680–2715, doi:10.3762/bjoc.17.182

Graphical Abstract
  • accompanied by coupling nucleobases via N-glycosylation. However, over the last three decades, efforts were made for the synthesis of 1,3-oxathiolane nucleosides by selective N-glycosylation of carbohydrate precursors at C-1, and this approach has emerged as a strong alternative that allows simple
  • -oxathiolane ring with different nucleobases in a way that only one isomer is produced in a stereoselective manner via N-glycosylation. An emphasis has been placed on the C–N-glycosidic bond constructed during the formation of the nucleoside analogue. The third focus is on the separation of enantiomers of 1,3
  • -oxathiolane nucleosides via resolution methods. The chemical as well as enzymatic procedures are reviewed and segregated in this review for effective synthesis of 1,3-oxathiolane nucleoside analogues. Keywords: chiral auxiliaries; enzymes; Lewis acids; N-glycosylation; 1,3-oxathiolane sugar and nucleosides
PDF
Album
Review
Published 04 Nov 2021

Halides as versatile anions in asymmetric anion-binding organocatalysis

  • Lukas Schifferer,
  • Martin Stinglhamer,
  • Kirandeep Kaur and
  • Olga García Macheño

Beilstein J. Org. Chem. 2021, 17, 2270–2286, doi:10.3762/bjoc.17.145

Graphical Abstract
  • macrocycle 81 (Scheme 17a) [78]. Compared to bis-thiourea 80, the higher rigidity in the macrocycle 81 not only enforces halide abstraction significantly, but also allowed for a better control of the stereoselectivity in the glycosylation of glycosyl halides 78 with a variety of coupling partners. In this
  • diastereoselective glycosylation reaction. b) Competing SN1 vs SN2 reactivity. a) Folding mechanism of oligotriazoles upon anion recognition. b) Representative tetratriazole 82 catalyzed enantioselective Reissert-type reaction of quinolines and pyridines with various nucleophiles. Switchable chiral tetratriazole
PDF
Album
Review
Published 01 Sep 2021

Progress and challenges in the synthesis of sequence controlled polysaccharides

  • Giulio Fittolani,
  • Theodore Tyrikos-Ergas,
  • Denisa Vargová,
  • Manishkumar A. Chaube and
  • Martina Delbianco

Beilstein J. Org. Chem. 2021, 17, 1981–2025, doi:10.3762/bjoc.17.129

Graphical Abstract
  • polymerization [18], C) chemical synthesis. The use of enzymes has undeniable advantages because it offers the possibility to use unprotected sugars as substrates and guarantees remarkable control of the regio- and stereoselectivity during glycosylation. Mono- or oligosaccharides bearing a reactive leaving group
  • only small modifications, hampering the formation of unnatural polymers. Low glycosylation yields and product hydrolysis represent additional hurdles associated with enzymatic synthesis of polysaccharides [23]. With this approach, homopolymers are often obtained as non-uniform samples, because the
  • synthetic steps. In general, BBs are equipped with a reactive anomeric LG to allow for glycosylation and suitable PGs to ensure regio- and stereocontrol [25]. Even though, in most cases, BB preparation follows straightforward protection/deprotection strategies, the low selectivity and yield of certain
PDF
Album
Review
Published 05 Aug 2021

Sustainable manganese catalysis for late-stage C–H functionalization of bioactive structural motifs

  • Jongwoo Son

Beilstein J. Org. Chem. 2021, 17, 1733–1751, doi:10.3762/bjoc.17.122

Graphical Abstract
  • peptide, which can be further utilized as a Michael acceptor for a variety of nucleophiles. Based on their manganese-catalyzed allylation using Morita–Baylis–Hillman carbonates, the Ackermann group established an applicable late-stage C–H glycosylation of peptides (Scheme 12) [95]. Thus, allylative
  • , a natural product scaffold, was transformed into glycosylated tryptophan 31f. It is noteworthy that this manganese(I)-catalyzed glycoconjugation method avoids racemization. Furthermore, manganese-catalyzed allylative linchpin C–H glycosylation was investigated using structurally sophisticated
  • adjacent directing group (see 31h). This manganese(I)-catalyzed late-stage glycosylation provides hexaglycopeptide conjugate 31m without epimerization. Moreover, the late-stage C–H diversification process enabled bioorthogonal access to glycosylated peptides, such as a fluorescent BODIPY-labeled tryptophan
PDF
Album
Review
Published 26 Jul 2021

A systems-based framework to computationally describe putative transcription factors and signaling pathways regulating glycan biosynthesis

  • Theodore Groth,
  • Rudiyanto Gunawan and
  • Sriram Neelamegham

Beilstein J. Org. Chem. 2021, 17, 1712–1724, doi:10.3762/bjoc.17.119

Graphical Abstract
  • , State University of New York, Buffalo, NY 14260, USA 10.3762/bjoc.17.119 Abstract Glycosylation is a common posttranslational modification, and glycan biosynthesis is regulated by a set of glycogenes. The role of transcription factors (TFs) in regulating the glycogenes and related glycosylation
  • relate cell-signaling pathways to TFs and cellular glycosylation state. Whereas analysis results are presented for all 29 cancer types, specific focus is placed on human luminal and basal breast cancer disease progression. Overall, the article presents a computational approach to describe TF–glycogene
  • relationships, the starting point for experimental system-wide validation. Keywords: ChIP-Seq; glycoinformatics; glycosylation; TCGA transcription factor; Introduction The glycan signatures of cells and tissue are controlled by the expression pattern of 300–350 glycosylating-related genes that are together
PDF
Album
Supp Info
Full Research Paper
Published 22 Jul 2021

Chemical synthesis of C6-tetrazole ᴅ-mannose building blocks and access to a bioisostere of mannuronic acid 1-phosphate

  • Eleni Dimitriou and
  • Gavin J. Miller

Beilstein J. Org. Chem. 2021, 17, 1527–1532, doi:10.3762/bjoc.17.110

Graphical Abstract
  • approach to provide structurally defined building blocks containing bioisosteres of ᴅ-mannuronic acid. Building on our recently reported synthesis and glycosylation capability of hydroxamate-modified ᴅ-mannuronate building blocks [11], we now demonstrate the synthesis of a second carboxylate C6-bioisostere
  • for glycosylation of 3-(benzyloxycarbonylamino)-1-propanol and furnished a regioisomeric and anomeric mixture in low yield (34%, with 20% recovered starting material and 18% hydrolysed donor, 3:1, α/β). The β-linked (minor) anomer was identified through 1JC-H coupling constant data (J = 156 Hz
  • ), similar to products obtained using C6-mannuronate and C6-hydroxamate donors [11]. This initial result suggests a reduced capability using C6-tetrazole donors with a primary alcohol acceptor; comparative yields for glycosylation of 3-bromopropanol using C6-hydroxamate and C6-mannuronate donors were 65–85
PDF
Album
Supp Info
Letter
Published 05 Jul 2021

Synthesis of multiply fluorinated N-acetyl-D-glucosamine and D-galactosamine analogs via the corresponding deoxyfluorinated glucosazide and galactosazide phenyl thioglycosides

  • Vojtěch Hamala,
  • Lucie Červenková Šťastná,
  • Martin Kurfiřt,
  • Petra Cuřínová,
  • Martin Dračínský and
  • Jindřich Karban

Beilstein J. Org. Chem. 2021, 17, 1086–1095, doi:10.3762/bjoc.17.85

Graphical Abstract
  • resulting from the low stability of amino sugar hemiacetals. The prepared polyfluorinated thiodonors and hemiacetals are valuable intermediates in oligosaccharide synthesis and their utility in glycosylation is currently being studied in our group. Retrosynthetic analysis of the target fluoro analogs
PDF
Album
Supp Info
Full Research Paper
Published 11 May 2021

Metal-free glycosylation with glycosyl fluorides in liquid SO2

  • Krista Gulbe,
  • Jevgeņija Lugiņina,
  • Edijs Jansons,
  • Artis Kinens and
  • Māris Turks

Beilstein J. Org. Chem. 2021, 17, 964–976, doi:10.3762/bjoc.17.78

Graphical Abstract
  • covalently bind Lewis basic fluoride ions in a relatively stable fluorosulfite anion (FSO2−). Herein we report the application of liquid SO2 as a promoting solvent for glycosylation with glycosyl fluorides without any external additive. By using various temperature regimes, the method is applied for both
  • during the glycosylation with glycosyl fluorides in liquid SO2 is proved by 19F NMR spectroscopy. A sulfur dioxide-assisted glycosylation mechanism that proceeds via solvent separated ion pairs is proposed, whereas the observed α,β-selectivity is substrate-controlled and depends on the thermodynamic
  • equilibrium. Keywords: fluorosulfite; glycosyl fluoride; Lewis acid; liquid sulfur dioxide; metal-free glycosylation; Introduction The glycosylation reaction is still one of the most important and basic synthetic strategies in carbohydrate chemistry that provides access to the various types of
PDF
Album
Supp Info
Full Research Paper
Published 29 Apr 2021

Simulating the enzymes of ganglioside biosynthesis with Glycologue

  • Andrew G. McDonald and
  • Gavin P. Davey

Beilstein J. Org. Chem. 2021, 17, 739–748, doi:10.3762/bjoc.17.64

Graphical Abstract
  • O-linked glycosylation, with a web-based application, O-Glycologue, that allows knockouts of enzymes of O-linked glycosylation and the assignment of custom “wild type” sets of enzyme activities to study the effects of differential knockouts on the resultant networks [15]. In this article, we
PDF
Album
Full Research Paper
Published 23 Mar 2021

Chemical constituents of Chaenomeles sinensis twigs and their biological activity

  • Joon Min Cha,
  • Dong Hyun Kim,
  • Lalita Subedi,
  • Zahra Khan,
  • Sang Un Choi,
  • Sun Yeou Kim and
  • Chung Sub Kim

Beilstein J. Org. Chem. 2020, 16, 3078–3085, doi:10.3762/bjoc.16.257

Graphical Abstract
  • configuration at C-6 was deduced as S (the stereochemical descriptor was flipped from R to S due to an O-glycosylation at C-2, see Figure 2C, right). The 9R configuration of 1 was determined by the modified Mosher’s method [23][24][25]. The hydrolysis product of 1 (1a) was esterified with the Mosher reagents
PDF
Album
Supp Info
Letter
Published 17 Dec 2020

Semiautomated glycoproteomics data analysis workflow for maximized glycopeptide identification and reliable quantification

  • Steffen Lippold,
  • Arnoud H. de Ru,
  • Jan Nouta,
  • Peter A. van Veelen,
  • Magnus Palmblad,
  • Manfred Wuhrer and
  • Noortje de Haan

Beilstein J. Org. Chem. 2020, 16, 3038–3051, doi:10.3762/bjoc.16.253

Graphical Abstract
  • compared to Skyline, and GlycopeptideGraphMS. All quantification packages resulted in comparable glycosylation profiles but featured differences in terms of robustness and data quality control. Partial cysteine oxidation was identified as an unexpectedly abundant peptide modification and impaired the
  • quantification. Keywords: bioinformatics; cysteine oxidation; glycoproteomics; immunoglobulins; mass spectrometry; Introduction Protein glycosylation mainly occurs in the form of N- and O-glycosylation. N-Glycans are attached to Asn within an amino acid consensus sequence (Asn-Xxx-Ser/Thr, Xxx ≠ Pro) and O
  • features, such as the linkage position and anomeric configuration, make protein glycosylation a highly complex posttranslational modification (PTM). Glycoproteomics has become important for many life science disciplines, in particular for biomedical and biopharmaceutical research [3][4][5]. Glycopeptide
PDF
Album
Supp Info
Full Research Paper
Published 11 Dec 2020

A consensus-based and readable extension of Linear Code for Reaction Rules (LiCoRR)

  • Benjamin P. Kellman,
  • Yujie Zhang,
  • Emma Logomasini,
  • Eric Meinhardt,
  • Karla P. Godinez-Macias,
  • Austin W. T. Chiang,
  • James T. Sorrentino,
  • Chenguang Liang,
  • Bokan Bao,
  • Yusen Zhou,
  • Sachiko Akase,
  • Isami Sogabe,
  • Thukaa Kouka,
  • Elizabeth A. Winzeler,
  • Iain B. H. Wilson,
  • Matthew P. Campbell,
  • Sriram Neelamegham,
  • Frederick J. Krambeck,
  • Kiyoko F. Aoki-Kinoshita and
  • Nathan E. Lewis

Beilstein J. Org. Chem. 2020, 16, 2645–2662, doi:10.3762/bjoc.16.215

Graphical Abstract
  • compliance with FAIR standards. Here, we present Linear Code for Reaction Rules (LiCoRR), version 1.0, an unambiguous representation for describing glycosylation reactions in both literature and code. Keywords: glycoinformatics; linear code; systems glycobiology; Introduction Glycans are predominantly
  • development, exchange, extension, and validation of glycosylation models and analysis tools. Here we bring explicit attention to the concerns we raise above, we provide a focused, text-based representation of reaction rules that have been introduced for the purpose of formalizing these communications. GlycoCT
  • , cytoplasm (bacteria and archaea), or lysosome (degradation, Man-6-P dephosphorylation and lysosomal glycoprotein biosynthesis [33][34] or paucimannose recycling [35]), are important constraints on glycosylation [36], therefore, the addition of this information to the Linear Code reaction rules provides
PDF
Album
Supp Info
Commentary
Published 27 Oct 2020

Anion exchange resins in phosphate form as versatile carriers for the reactions catalyzed by nucleoside phosphorylases

  • Julia N. Artsemyeva,
  • Ekaterina A. Remeeva,
  • Tatiana N. Buravskaya,
  • Irina D. Konstantinova,
  • Roman S. Esipov,
  • Anatoly I. Miroshnikov,
  • Natalia M. Litvinko and
  • Igor A. Mikhailopulo

Beilstein J. Org. Chem. 2020, 16, 2607–2622, doi:10.3762/bjoc.16.212

Graphical Abstract
  • were tested in the synthesis of nelarabine, kinetin riboside, and cladribine with good to excellent yields (52–93%). Keywords: anion exchange resins; N6-benzyladenosine; cladribine; enzymatic glycosylation; kinetin riboside; nelarabine; α-ᴅ-pentofuranose-1-phosphates; phosphorolysis of nucleosides
  • cited therein). The classical two-stage version of the enzymatic transglycosylation reaction [16][17][18][19][20], as well as one-pot synthesis, and the more sophisticated option employing two cross-glycosylation transformations for nucleoside synthesis [23][24][25][26][27], seemed less attractive and
  • more complicated in comparison with the enzymatic reaction of a heterocyclic base with an individual PF-1Pi [17][18][27]. However, it is known that most of purine heterocycles are poorly soluble in aqueous phosphate buffers, and the use of a cross-glycosylation scheme, i.e., a purine nucleoside as a
PDF
Album
Supp Info
Full Research Paper
Published 22 Oct 2020

Comparative ligand structural analytics illustrated on variably glycosylated MUC1 antigen–antibody binding

  • Christopher B. Barnett,
  • Tharindu Senapathi and
  • Kevin J. Naidoo

Beilstein J. Org. Chem. 2020, 16, 2540–2550, doi:10.3762/bjoc.16.206

Graphical Abstract
  • analysis were carried out. These analyses were used to rapidly assess key features of the system, interrogate the dynamic structure of the ligand, and determine the role of glycosylation on the conformational equilibrium. The glycopeptide conformations in solution change relative to the peptide; thus a
  • sequence of 20 amino acids (–His-Gly-Val-Thr-Ser-Ala-Pro-Asp-Thr-Arg-Pro-Ala-Pro-Gly-Ser-Thr-Ala-Pro-Pro-Ala–)n, and there are five sites where O-glycosylation may occur (indicated in bold). In cancerous cells, the glycans tend to be truncated or have additional sialylation [14]. For example, in mammary
  • are commonly associated with cancerous cells [14]. Movahedin et al. confirmed that the glycosylation of MUC1 influences its binding to the AR20.5 murine antibody [16], specifically the Tn-antigen binds more strongly than the nonglycosylated antigen. AR20.5 is known to bind a specific epitope within
PDF
Album
Supp Info
Full Research Paper
Published 13 Oct 2020
Other Beilstein-Institut Open Science Activities